Poly(3,3′-dibromo-2,2′-bithiophene)(PBr₂BT) and poly(3,3′-dichloro-2,2′-bithiophene)(PCl₂BT) can be readily deposited on electrodes via electrochemical polymerization of the respective monomers. Visible cracks observed on the resulting PCl₂BT and PBr₂BT films were related to the steric influence of the substituents. The redox potentials of polymers were found to decrease in the order PBr₂BT PCl₂BT > poly(bithiophene)(PBT), suggesting that the steric hindrance and electronegative nature of the halogen groups impart a negative effect on the inculator-to-conductor transition in PBr₂BT and PCl₂BT. In addition, the less extended π-conjugation, together with the electrochemically unfavourable doped state and discontinuous macroscopic structure, prevent the solid-state PBr₂BT and PCl₂BT from achieving conductivity comparable to the parent PBT. However, the enhanced solubility with consequent improved processibility, coupled with the presence of reactive pendant halogens would make these systems useful as functional polymers for further modifications in the post-polymerization stage.